The Danger of Asking Too Many, or Too Few, Sales Questions

Back before the days of Internet searches, salespeople could start conversations with, “Tell me about your business and what keeps you up at night.” Now, the answer would be: “I’m not here to educate you. I don’t have time to be your onboarding department. You’re supposed to know this stuff.”

If you ask sales questions that are too basic, to which you would have known the answer if you’d done your homework, you risk annoying the customer. And, if you ask too many questions, even good ones, one after another, it becomes an interrogation.

In sales dialogues, there needs to be a balance between asking good sales questions and providing good insights. The customer doesn’t have the time or the patience to do what essentially is onboarding, but they often make time to reason together if you bring them value and provoke thought in meaningful ways.

The catch with insights is that you can’t sound perceptive without the right sales questioning strategy. If you ask too few questions, you can end up presupposing things that may or may not be true. You also risk coming across as arrogant or self-servicing in your insights.

A better approach is illustrated by the Sales Conversation Pendulum, which swings between asking and sharing question-led dialogue and insight-led dialogue. In between the two is the essential skill of listening.

Listening is a critical skill that just makes common sense. Although, as the saying goes, common sense is not so common. It’s certainly not common practice. If you go into a meeting with six great questions on a topic, but after the first one, the customer indicates that’s not an area of interest, it’s madness to go forward with the next five questions in your pocket. That’s why listening is one of Richardson Sales Performance’s Six Critical Skills, along with questioning, checking, relating, presence, and positioning.

An effective process involves asking open-ended questions, listening, checking, and so on. It takes planning and practice, especially when wild cards are thrown in. Salespeople need to be able to react in the moment, and being able to switch from Plan A to Plan B becomes seamless when these critical skills are second nature.

Gauging how well your questioning strategy is going in real time also includes the ability to read body language. That’s why face-to-face meetings are preferable to conference calls. When sitting in front of a group of decision-makers, it’s easy to see the interactions between people in the meeting. Are they looking at you, at each other, or at their watches? You can tell if they’re paying attention and engaged or whether you’re missing the mark.

By watching body language, you can follow the reactions and interactions as you drill down in your sales questioning strategy. You want to make sure you’re asking two or three layers of clarifying questions to make sure you understand not only what they’re saying but what they actually mean — and to confirm that what those words mean to you reflect what they mean to customers. If, for example, someone says, “I want this initiative to be highly successful,” my response would be, “Tell me what the desired level of success looks like to you.”

That kind of checking is important because we may have totally different ways of defining success. Asking a clarifying, follow-up question makes sure that we’re both on the same page looking for the same result.

Asking, listening, clarifying, providing insights — it all sounds easy in theory, and it can be. All it takes is planning, preparation, and practice of your sales questioning strategy — over and over again.